Tag: 200-300

Mixed-Linker Isoreticular Zn(II) Metal-Organic Frameworks as Bronsted Acid-Base Bifunctional Catalysts for Knoevenagel Condensation Reactions was written by Huang, Guo-Quan;Chen, Jun;Huang, Yong-Liang;Wu, Kun;Luo, Dong;Jin, Ji-Kang;Zheng, Ji;Xu, Shi-Hai;Lu, Weigang. And the article was included in Inorganic Chemistry in 2022.Application of 55490-87-4 This article mentions the following:

Multicomponent metal-organic frameworks (MOFs) have received an increasing amount of attention due to their potential to produce new topologies, pore metrics, and functionalities compared to MOFs with a single metal cluster and one organic linker. Herein, five isoreticular Zn MOFs were obtained by mixing two types of linear ditopic linkers in a one-pot solvothermal synthesis. Interestingly, in the resulting Zn MOFs a six-connected cyclic trinuclear Zn(II) cluster and an eight-connected linear trinuclear Zn(II) cluster coexist, leading to an uncommon (6,8)-connected network. Catalytic activities toward the solvent-free Knoevenagel reactions were observed for all of these MOFs. Further exptl. and computational studies suggest that they are Bronsted acid-base bifunctional catalysts. Through chem. modifications of dicarboxylate ligands, including their aromatic backbones and substituents, we have successfully implemented reticular chem. for the modulations of pore sizes, surface areas, and catalytic performances in a series of four-component isoreticular MOFs. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Application of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Application of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Heterogeneous cobalt catalysts for reductive amination with H₂: general synthesis of secondary and tertiary amines was written by Mao, Fei;Sui, Dejun;Qi, Zhengliang;Fan, Haipeng;Chen, Rizhi;Huang, Jun. And the article was included in RSC Advances in 2016.Reference of 10282-32-3 This article mentions the following:

Heterogeneous Co@NC catalysts were prepared, characterized and applied for the reductive amination of aldehydes and ketones with H₂ gas. The Co catalyst Co@NC (800-2 h) was found to be active and selective for the reductive amination of aldehydes and ketones using H₂ gas. Thus, general synthesis of secondary and tertiary amines was developed by the Co-catalyzed reductive amination with H₂ gas, and various secondary and tertiary amines was obtained in high yields. Moreover, a practical synthesis of N-substituted isoindolinones was also presented by a one step process with the Co@NC (800-2 h) catalyst. The Co@NC (800-2 h) catalyst was reusable at least five times without evident loss of activity. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Reference of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Reference of 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A new and practical method for the synthesis of 6-aryl-5,6-dihydropyrido[2,3-d]pyrimidine-4,7(3H,8H)-diones was written by Camarasa, Marta;Barnils, Christian;Puig de la Bellacasa, Raimon;Teixido, Jordi;Borrell, Jose I.. And the article was included in Molecular Diversity in 2013.Quality Control of 2-(2,6-Dibromophenyl)acetonitrile This article mentions the following:

A one step general synthetic method for the synthesis of 6-aryl-5,6-dihydropyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione derivatives was described. This methodol. is based on treating a 2-aryl-substituted acrylate with a 6-amino-4(3H)-pyrimidinone derivative in the presence of a base under microwave irradiation conditions. The resulting pyrido[2,3-d]pyrimidine derivatives present an aryl substituent at position C6, precisely the one directly related to the biol. activity of such heterocyclic compounds These protocols were extended to other 2-alkyl-substituted and 3-alkyl (or aryl)-substituted acrylate derivatives but with lower yields. The synthesis of the target compounds was achieved by a reaction of 2,6-diamino-4(3H)-pyrimidinone with α-(methylene)benzeneacetic acid Me ester derivatives (acrylate esters), α-methylene-1-naphthaleneacetic acid Me ester, 2-methyl-2-propenoic acid Me ester. 6-Amino-2-(methylthio)-4(3H)-pyrimidinone was also a suitable starting material. The title compounds thus formed included 2-amino-5,8-dihydro-6-(phenyl)pyrido[2,3-d]pyrimidine-4,7(3H,6H)-dione (I) and related substances. In the experiment, the researchers used many compounds, for example, 2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9Quality Control of 2-(2,6-Dibromophenyl)acetonitrile).

2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Quality Control of 2-(2,6-Dibromophenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Phosphino-amine (PN) Ligands for Rapid Catalyst Discovery in Ruthenium-Catalyzed Hydrogen-Borrowing Alkylation of Anilines: A Proof of Principle was written by Broomfield, Lewis Marc;Wu, Yichen;Martin, Eddy;Shafir, Alexandr. And the article was included in Advanced Synthesis & Catalysis in 2015.Quality Control of 4-(Benzylamino)benzonitrile This article mentions the following:

A general synthetic protocol for the synthesis of simple phosphino-amine (PN) ligands is described with 19 ligands being isolated in good yields. High-throughput ligand screening uncovered the success of two of these ligands for aromatic amine alkylations via ruthenium-catalyzed hydrogen borrowing reactions. The combination of N,N’-bis(diphenylphosphino)-N,N’-dimethylpropylenediamine with a ruthenium(II) source and potassium hydroxide (15 mol%) is the optimal system for selective monobenzylations of aromatic amines (method A). Over 70% isolated yields have been achieved for the formation of 14 secondary aromatic amines under mild reaction conditions (120° and 1.05 equivalent of benzyl alc.). On the other hand, N,N-bis(diphenylphosphino)-isopropylamine was the ligand utilized for both selective monomethylation and monoethylation reactions of aromatic amines (method B). Here the alc. is charged as both the reaction medium and substrate and 9 examples are disclosed with all isolated yields exceeding 70%. These methods have been applied to the synthesis of important synthetic building blocks based on aminoferrocene. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Quality Control of 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Quality Control of 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A study of the relationship between the chemical structures and the fluorescence quantum yields of coumarins, quinoxalinones and benzoxazinones for the development of sensitive fluorescent derivatization reagents was written by Azuma, Kentaro;Suzuki, Sachiko;Uchiyama, Seiichi;Kajiro, Toshi;Santa, Tomofumi;Imai, Kazuhiro. And the article was included in Photochemical & Photobiological Sciences in 2003.Recommanded Product: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

To develop new fluorescent derivatization reagents, we investigated the relationship between the chem. structures and the fluorescence quantum yields (Φ_f) of coumarins, quinoxalinones and benzoxadinones. Forty-six compounds were synthesized and their fluorescence spectra were measured in n-hexane, Et acetate, methanol and water. The energy levels of these compounds were calculated by combination of the semi-empirical AM1 and INDO/S (CI = all) methods. The ΔE(T_n(n,π*), S₁(π,π*)) (the energy gap between the T_n(n,π*) and S₁(π,π*) states) values were well correlated with the Φ_f values, which enables us to predict the Φ_f values from their chem. structures. Based on this relationship, 3-phenyl-7-N-piperazinoquinoxalin-2(1H)-one (PQ-Pz) and 7-(3-(S)-aminopyrrolidin-1-yl)-3-phenylquinoxalin-2-(1H)-one (PQ-APy) were developed as fluorescent derivatization reagents for carboxylic acids. The derivatives of the carboxylic acids with PQ-Pz and PQ-APy showed large Φ_f values even in polar solvents, suggesting that these reagents are suitable for the microanal. of biol. important carboxylic acids by reversed phase HPLC. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Recommanded Product: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Recommanded Product: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of intermediate of strontium ranelate by using ionic liquid as phase transfer catalyst was written by Li, Cen;Jiang, Yi;Jiang, Ye;Liu, Feng-hua. And the article was included in Huaxi Yaoxue Zazhi in 2009.Application of 58168-20-0 This article mentions the following:

OBJECTIVE: To study a new catalytic way using ionic liquid as phase transfer catalyst for the synthesis of intermediate of strontium ranelate. METHODS: Tetra-Et ester of 5-aminothiophene was synthesized from 5-aminothiophene using Et bromoacetate as alkylating reagent and ionic liquid as phase transfer catalyst. RESULTS and CONCLUSION: The proposed method was not only suitable for industrial manufacture with high yield of 81%, but also could cut down the discharging of pollutants. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Application of 58168-20-0).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Application of 58168-20-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Photoelectrochemical and thermal characterization of aromatic hydrocarbons substituted with a dicyanovinyl unit was written by Kotowicz, Sonia;Sek, Danuta;Kula, Slawomir;Fabianczyk, Aleksandra;Malecki, Jan Grzegorz;Gnida, Pawel;Mackowski, Sebastian;Siwy, Mariola;Schab-Balcerzak, Ewa. And the article was included in Dyes and Pigments in 2020.Safety of 2-(Anthracen-9-ylmethylene)malononitrile This article mentions the following:

Seven aromatic hydrocarbons bearing a dicyanovinyl unit were prepared to determine the relation between both the number of aromatic rings and location of acceptor substituent on their thermal and optoelectronic properties. Addnl., the d. functional theory calculations were performed. The obtained compounds showed temperatures of the beginning of thermal decomposition in the range of 137-289°, being above their resp. m.ps. found between 88 and 248°. They were electrochem. active and showed quasi-reversible reduction process, except for 2-(phen-1-yl)methylene malononitrile. Electrochem. estimated energy band gaps were below 3.0 eV, in the range of 2.10-2.50 eV. The absorption and emission spectra were recorded in CHCl₃ and NMP and in solid state. All compounds strongly absorbed radiation with absorption maximum ranging from 307 to 454 nm ascribed to the intramol. charge transfer between the donor and acceptor units. The aromatic hydrocarbons were luminescent in all investigated media and exhibited higher photoluminescence quantum yields in the solid state due to the aggregation induced emission phenomena. Electroluminescence ability of selected compounds was tested in a diode with guest-host configuration. Addnl., the selected compound together with a com. N719 was applied in the dye-sensitized solar cell. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Safety of 2-(Anthracen-9-ylmethylene)malononitrile).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Safety of 2-(Anthracen-9-ylmethylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A Base- and Metal-free Protocol for the Synthesis of 2-Aryl/heteroaryl Thiazolines was written by Chaudhary, Shweta;Milton, Marilyn D.;Garg, Parul. And the article was included in ChemistrySelect in 2017.Formula: C12H14N2O This article mentions the following:

A simple and efficient base- and metal-free protocol for the synthesis of 2-aryl/heteroarylthiazolines I [Ar = 4-BrC₆H₄, 4-n-BuHNCH₂C₆H₄, 2-pyridyl, etc.; R = H, CO₂Et] from aryl/heteroaryl nitriles and cysteamine hydrochloride was reported. This method was applicable to a series of aryl/heteroaryl nitriles containing different substituents such as halides, amines, substituted azoles, etc. and furnishing the corresponding thiazolines in up to 99% yields. A selective synthesis of mono- or bis-thiazoline in more than 90% yield was also observed by modifying the duration of the reaction. A probable reaction mechanism involving the formation of highly activated arylimino chloride was also given. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Formula: C12H14N2O).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Formula: C12H14N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mechanistic investigation of the iridium-catalysed alkylation of amines with alcohols was written by Fristrup, Peter;Tursky, Matyas;Madsen, Robert. And the article was included in Organic & Biomolecular Chemistry in 2012.Quality Control of 4-(Benzylamino)benzonitrile This article mentions the following:

The [Cp*IrCl₂]₂-catalyzed alkylation of amines with alcs. was investigated using a combination of exptl. and theor. methods. A Hammett study involving a series of para-substituted benzyl alcs. resulted in a line with a neg. slope. This clearly documents that a pos. charge is built up in the transition state, which in combination with the measurement of a significant kinetic isotope effect determines hydride abstraction as being the selectivity-determining step under these conditions. A complementary Hammett study using para-substituted anilines was also carried out. Again, a line with a neg. slope was obtained suggesting that nucleophilic attack on the aldehyde is selectivity-determining A computational investigation of the entire catalytic cycle with full-sized ligands and substrates was performed using d. functional theory. The results suggest a catalytic cycle where the intermediate aldehyde stays coordinated to the iridium catalyst and reacts with the amine to give a hemiaminal which is also bound to the catalyst. Dehydration to the imine and reduction to the product amine also takes place without breaking the coordination to the catalyst. The fact that the entire catalytic cycle takes place with all the intermediates bound to the catalyst is important for the further development of this synthetic transformation. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Quality Control of 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Quality Control of 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Oxidation of alcohols by transition metal complexes. Part III. The reduction of aldimines by hydrogen transfer from propan-2-ol catalyzed by rhodium complexes was written by Grigg, Ronald;Mitchell, Thomas R. B.;Tongpenyai, Ngampong. And the article was included in Synthesis in 1981.Category: nitriles-buliding-blocks This article mentions the following:

Benzaldimines 4-RC₆H₄CH:NCH₂Ph (R = H, Me, MeO, Cl, CF₃) and I (R¹ = H, MeO, Cl, CF₃, cyano; R² = H, MeO, Cl, CF₃, cyano) reacted with Me₂CHOH and a Rh complex to yield the resp. 4-RC₆H₄CH₂NHCH₂Ph and II. A mixture of PhCH:NCH₂Ph, RhCl(PPh₃)₃, and Na₂CO₃ in Me₂CHOH was refluxed 60 min to give ∼90% (Ph₂CH₂)₂NH. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Category: nitriles-buliding-blocks).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts